PL171878B1 - wyzszych kwasów tluszczowych PL - Google Patents
wyzszych kwasów tluszczowych PLInfo
- Publication number
- PL171878B1 PL171878B1 PL93298214A PL29821493A PL171878B1 PL 171878 B1 PL171878 B1 PL 171878B1 PL 93298214 A PL93298214 A PL 93298214A PL 29821493 A PL29821493 A PL 29821493A PL 171878 B1 PL171878 B1 PL 171878B1
- Authority
- PL
- Poland
- Prior art keywords
- reaction mixture
- reactor
- catalyst
- transesterification
- temperature
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 62
- 125000005907 alkyl ester group Chemical group 0.000 title claims abstract description 8
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 8
- 239000000194 fatty acid Substances 0.000 title claims abstract description 8
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 8
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 102
- 235000011187 glycerol Nutrition 0.000 claims abstract description 45
- 239000011541 reaction mixture Substances 0.000 claims abstract description 37
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 33
- 239000003054 catalyst Substances 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 238000000605 extraction Methods 0.000 claims abstract description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000000243 solution Substances 0.000 claims abstract description 14
- 239000000344 soap Substances 0.000 claims abstract description 13
- 238000005406 washing Methods 0.000 claims abstract description 11
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 150000001298 alcohols Chemical class 0.000 claims abstract description 6
- 239000003921 oil Substances 0.000 claims description 15
- 238000000926 separation method Methods 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 9
- 239000007853 buffer solution Substances 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 3
- 239000003925 fat Substances 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000008366 buffered solution Substances 0.000 claims description 2
- 238000010924 continuous production Methods 0.000 claims description 2
- 235000021588 free fatty acids Nutrition 0.000 claims description 2
- 239000012487 rinsing solution Substances 0.000 claims description 2
- 150000003626 triacylglycerols Chemical class 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 36
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 239000011536 extraction buffer Substances 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 235000019198 oils Nutrition 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002283 diesel fuel Substances 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 235000019484 Rapeseed oil Nutrition 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- -1 fatty acid esters Chemical class 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N ethyl trimethyl methane Natural products CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 238000009884 interesterification Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 235000019489 Almond oil Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002551 biofuel Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000010710 diesel engine oil Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Liquid Carbonaceous Fuels (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4209779A DE4209779C1 (enrdf_load_stackoverflow) | 1992-03-26 | 1992-03-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL298214A1 PL298214A1 (en) | 1994-01-24 |
| PL171878B1 true PL171878B1 (pl) | 1997-06-30 |
Family
ID=6455033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL93298214A PL171878B1 (pl) | 1992-03-26 | 1993-03-24 | wyzszych kwasów tluszczowych PL |
Country Status (11)
Families Citing this family (106)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5710030A (en) * | 1995-09-13 | 1998-01-20 | Henkel Corporation | Process for preparing fuels, fuel substitutes, and fuel supplements from renewable resources |
| FR2748490B1 (fr) * | 1996-05-07 | 1998-06-19 | Inst Francais Du Petrole | Procede de fabrication d'esters ethyliques |
| DE19702989A1 (de) * | 1997-01-28 | 1998-07-30 | Clariant Gmbh | Umweltfreundlicher Dieseltreibstoff |
| DE19742097C1 (de) * | 1997-09-24 | 1998-12-10 | Henkel Kgaa | Verfahren zur Gewinnung von hellfarbigen Fettsäureniedrigalkylestern mit vermindertem Gehalt an freiem und gebundenem Glycerin |
| DE19925871A1 (de) | 1999-06-07 | 2000-12-21 | At Agrar Technik Gmbh | Verfahren zur Herstellung von Fettsäureestern einwertiger Alkylalkohole und deren Verwendung |
| DE10132842C1 (de) * | 2001-07-06 | 2002-11-28 | Siegfried Peter | Verfahren zur Umesterung von Fett und/oder Öl mittels Alkoholyse |
| DE20113126U1 (de) * | 2001-08-14 | 2001-11-22 | Berger, Bruno, Braunau | Umesterungsvorrichtung mit Schrägrohrreaktor |
| US20050081435A1 (en) * | 2001-09-09 | 2005-04-21 | Lastella Joseph P. | Continuous flow method and apparatus for making biodiesel fuel |
| HU0104786D0 (en) | 2001-11-08 | 2002-01-28 | Kovacs Andras Dr | Method for producing of vegetable oil-methyl-esther |
| AUPR946201A0 (en) * | 2001-12-13 | 2002-01-24 | Jott Australia Pty. Ltd. | Process for production of fatty acid esters |
| AU2002347198B2 (en) * | 2001-12-13 | 2008-04-17 | Jott Australia Pty Ltd | Process for production of fatty acid esters |
| ES2201894B2 (es) * | 2002-01-18 | 2005-03-01 | Industrial Management, S.A | Procedimiento para producir combustibles biodiesel con propiedades mejoradas a baja temperatura. |
| KR100556337B1 (ko) * | 2002-02-05 | 2006-03-03 | 주식회사 가야에너지 | 단일단계 연속공정을 통한 고순도 지방산 알킬에스테르의제조방법 |
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| TWI324592B (en) * | 2002-11-28 | 2010-05-11 | Sulzer Chemtech Ag | A method for the esterification of a fatty acid |
| US8088183B2 (en) | 2003-01-27 | 2012-01-03 | Seneca Landlord, Llc | Production of biodiesel and glycerin from high free fatty acid feedstocks |
| US7806945B2 (en) * | 2003-01-27 | 2010-10-05 | Seneca Landlord, Llc | Production of biodiesel and glycerin from high free fatty acid feedstocks |
| US7871448B2 (en) * | 2003-01-27 | 2011-01-18 | Seneca Landlord, Llc | Production of biodiesel and glycerin from high free fatty acid feedstocks |
| US9725397B2 (en) | 2003-01-27 | 2017-08-08 | REG Seneca, LLC | Production of biodiesel and glycerin from high free fatty acid feedstocks |
| KR100566106B1 (ko) * | 2003-03-28 | 2006-03-30 | 한국에너지기술연구원 | 바이오디젤유의 제조방법 |
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| JP4567961B2 (ja) * | 2003-11-27 | 2010-10-27 | 株式会社レボインターナショナル | 油脂からのデイーゼル燃料油製造プロセス |
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| US7619104B2 (en) * | 2005-04-04 | 2009-11-17 | Renewable Products Development Laboratories, Inc. | Process for producing biodiesel or fatty acid esters from multiple triglyceride feedstocks |
| BRPI0503631B1 (pt) * | 2005-08-19 | 2015-07-21 | Petróleo Brasileiro S A Petrobras | Processo para a produção de biodiesel |
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| FR2890961B1 (fr) * | 2005-09-21 | 2007-11-23 | Inst Francais Du Petrole | Procede perfectionne de fabrication d'esters ethyliques a partir de corps gras d'origine naturelle |
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| BRPI0913099A2 (pt) | 2008-05-19 | 2019-09-24 | Univ Wayne State | métodos e catalizadores para preparar biodiesel a partir da transesterificação de óleo não refinados |
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| US9315756B2 (en) | 2012-04-06 | 2016-04-19 | Exxonmobil Research And Engineering Company | Bio-feeds based hybrid group V base stocks and method of production thereof |
| ES2744868T3 (es) | 2012-04-18 | 2020-02-26 | Corbion Biotech Inc | Aceites hechos a medida |
| MA34793B1 (fr) | 2012-06-28 | 2014-01-02 | Mascir Morrocan Foundation For Advanced Science Innovation & Res | Procédé pour augmenter le potentiel de production de biocarburant à partir de microalgues en utilisant des bio-modulateurs |
| WO2014041437A2 (en) | 2012-08-13 | 2014-03-20 | Hyperthermics Holding As | Production of biokerosene with hyperthermophilic organisms |
| US9090862B2 (en) | 2012-12-21 | 2015-07-28 | Ductor Oy | System and method for processing biological material |
| US10098371B2 (en) | 2013-01-28 | 2018-10-16 | Solazyme Roquette Nutritionals, LLC | Microalgal flour |
| BR112015026948A8 (pt) | 2013-04-26 | 2017-10-03 | Solazyme Inc | "composições, lubrificante, tensoativo, solvente, formulação de limpeza, composição de borracha reticulável ou reticulada, tira de pneu, espuma de poliuretano e seu método de preparação |
| WO2014201001A1 (en) | 2013-06-11 | 2014-12-18 | Renewable Energy Group, Inc. | Production of biodiesel and products obtained therefrom |
| FR3009619B1 (fr) | 2013-08-07 | 2017-12-29 | Roquette Freres | Compositions de biomasse de microalgues riches en proteines de qualite sensorielle optimisee |
| US9328054B1 (en) | 2013-09-27 | 2016-05-03 | Travis Danner | Method of alcoholisis of fatty acids and fatty acid gyicerides |
| SG11201602638SA (en) | 2013-10-04 | 2016-05-30 | Solazyme Inc | Tailored oils |
| US9394550B2 (en) | 2014-03-28 | 2016-07-19 | Terravia Holdings, Inc. | Lauric ester compositions |
| US9969990B2 (en) | 2014-07-10 | 2018-05-15 | Corbion Biotech, Inc. | Ketoacyl ACP synthase genes and uses thereof |
| EP4071226A1 (en) | 2021-04-08 | 2022-10-12 | AT Agrar-Technik Int. GmbH | Process for producing fatty acid alkyl esters |
| WO2024017722A1 (en) | 2022-07-21 | 2024-01-25 | Basf Se | Mixed alkoxide catalyst for biodiesel production |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA517818A (en) * | 1955-10-25 | H. Kuhrt Noel | Process for substantially complete conversion of fatty material to partial ester | |
| JPS5665097A (en) * | 1979-05-30 | 1981-06-02 | Lion Corp | Manufacture of fatty acid lower alcohol ester |
| DE3444893A1 (de) * | 1984-12-08 | 1986-06-12 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung von fettsaeuremethylestern |
| DE3512497A1 (de) * | 1985-04-06 | 1986-10-09 | Hüls AG, 4370 Marl | Verfahren zur herstellung von carbonsaeurealkylestern, insbesondere fettsaeurealkylestern, und deren verwendung als dieselkraftstoff |
| DE3727081A1 (de) * | 1987-08-14 | 1989-02-23 | Merck Patent Gmbh | Beschichtungen |
| ATE99280T1 (de) * | 1989-04-05 | 1994-01-15 | Unilever Nv | Verfahren zum herstellen von niedrigalkylfettsaeuremonoester. |
| DE3932514A1 (de) * | 1989-09-29 | 1991-04-18 | Henkel Kgaa | Kontinuierliches verfahren zum herstellen niederer alkylester |
-
1992
- 1992-03-26 DE DE4209779A patent/DE4209779C1/de not_active Expired - Fee Related
-
1993
- 1993-02-18 MY MYPI93000275A patent/MY115277A/en unknown
- 1993-03-22 EP EP93104625A patent/EP0562504B1/de not_active Expired - Lifetime
- 1993-03-22 ES ES93104625T patent/ES2081152T3/es not_active Expired - Lifetime
- 1993-03-22 AT AT93104625T patent/ATE129695T1/de active
- 1993-03-22 DE DE59300838T patent/DE59300838D1/de not_active Expired - Lifetime
- 1993-03-22 DK DK93104625.4T patent/DK0562504T3/da active
- 1993-03-24 PL PL93298214A patent/PL171878B1/pl unknown
- 1993-03-25 BR BR9301318A patent/BR9301318A/pt not_active IP Right Cessation
- 1993-03-25 CA CA002092470A patent/CA2092470C/en not_active Expired - Lifetime
- 1993-03-26 US US08/037,224 patent/US5354878A/en not_active Expired - Lifetime
- 1993-03-26 CN CN93103664A patent/CN1041822C/zh not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US5354878A (en) | 1994-10-11 |
| CN1076687A (zh) | 1993-09-29 |
| CN1041822C (zh) | 1999-01-27 |
| ES2081152T3 (es) | 1996-02-16 |
| CA2092470C (en) | 1999-01-26 |
| ATE129695T1 (de) | 1995-11-15 |
| MY115277A (en) | 2003-05-31 |
| EP0562504A2 (de) | 1993-09-29 |
| DK0562504T3 (da) | 1996-03-04 |
| EP0562504B1 (de) | 1995-11-02 |
| EP0562504A3 (en) | 1993-10-27 |
| DE59300838D1 (de) | 1995-12-07 |
| PL298214A1 (en) | 1994-01-24 |
| DE4209779C1 (enrdf_load_stackoverflow) | 1993-07-15 |
| CA2092470A1 (en) | 1993-09-27 |
| BR9301318A (pt) | 1993-09-28 |
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